2-Pyridinemethanamine → HCID 53302604, compound
Reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.N1(C(N2C=CN=C2)=O)C=CN=C1.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][NH2:34]>C1COCC1>[OH:1][C:2]1[C:3]([C:12]([NH:34][CH2:33][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=2)=[O:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 8-hydroxyquinoline-7-carboxylic acid (100 mg, 0.53 mmol) and di(1H-imidazol-1-yl)methanone (86 mg, 0.53 mmol) in THF (5 mL) was heated to 60° C. for 3 h, under nitrogen. The reaction mixture was allowed to cool to RT and pyridin-2-ylmethanamine (46 mg, 0.424 mmol) was added. The resulting mixture was heated to 40° C. for 2 h and then stirred at RT. The reaction mixture was quenched with H2O and an aqueous saturated solution of sodium hydrogen carbonate, and twice extracted with DCM. The separated organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by SPE-SI cartridge (2 g, DCM to DCM:MeOH 99:1) affording the title compound (73 mg, 0.26 mmol) as a off-white solid.
Workup
- temperatureto cool to RT
- temperatureThe resulting mixture was heated to 40° C. for 2 h
- customThe reaction mixture was quenched with H2O
- extractionan aqueous saturated solution of sodium hydrogen carbonate, and twice extracted with DCM
- dry with materialThe separated organics were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by SPE-SI cartridge (2 g, DCM to DCM:MeOH 99:1)
Sources & evidence
- ORD record
- ord-1555f080a75a4414adbe276e194d13d0
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729076B2
Reaction notes
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